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. 2020 Sep 10:189:113432.
doi: 10.1016/j.jpba.2020.113432. Epub 2020 Jun 17.

Degradation profile of nepafenac in aqueous solution and structural characterization of a novel degradation product

Danilo Aleo  1 , Maria Grazia Saita  1 , Fabiola Spitaleri  1 , Claudia Sanfilippo  2 , Angela Patti  3
Affiliations

Degradation profile of nepafenac in aqueous solution and structural characterization of a novel degradation product

Danilo Aleo et al. J Pharm Biomed Anal. .

Abstract

The stability of the anti-inflammatory drug nepafenac was investigated in aqueous solutions containing hydroxypropyl-β-cyclodextrin at three different values of pH and degradation products were identified. (2-Amino-3-benzoyl)-oxoacetic acid, previously not reported as nepafenac-related impurity, was isolated and structurally characterized by NMR and ESI-MS analyses. It was also shown that the formation of this α-ketoacid from nepafenac in alkaline water/organic cosolvent solution occurs through an aerobic oxidation of the key intermediate 7-benzoyl-1,3-dihydro-indol-2-one, which in some extent is protected from oxidation in the presence of the cyclodextrin additive.

Keywords: Benzylic oxidation; Drug stability; HPLC; Nepafenac; α-Ketoacid.

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Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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